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Cyclic peptide melanocortin receptor ligands

a technology of melanocortin receptor and cyclic peptide, which is applied in the field of peptides, can solve the problems of increasing the risk of skin cancer and adrenal tissue carcinoma, and achieve the effect of reducing alcohol consumption

Inactive Publication Date: 2010-07-08
IPSEN PHARMA SAS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0066]In another aspect, the present invention provides a pharmaceutical composition comprising an effective amount of a compound of formula (I) as defined hereinabove, or a pharmaceutically acceptable salt thereof, together with a pharmaceutically-acceptable carrier or diluent, which is useful for decreasing appetite without compromising body weight. In yet another aspect, the present invention provides a pharmaceutical composition comprising an effective amount of a compound of formula (I) as defined hereinabove, or a pharmaceutically acceptable salt thereof, together with a pharmaceutically-acceptable carrier or diluent, useful for decreasing food consumption while increasing body weight.
[0091]In another aspect, the present invention provides a method of decreasing appetite without compromising body weight by administering an effective amount of a compound of formula (I) as defined hereinabove, or a pharmaceutically acceptable salt thereof. In another aspect, the present invention provides a method of decreasing food consumption while increasing body weight by administering an effective amount of a compound of formula (I) as defined hereinabove, or a pharmaceutically acceptable salt thereof.

Problems solved by technology

Agonism of the MC1-R receptor results in stimulation of the melanocytes which causes eumelanin and increases the risk for cancer of the skin.
Stimulation of MC2-R activity can result in carcinoma of adrenal tissue.

Method used

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  • Cyclic peptide melanocortin receptor ligands
  • Cyclic peptide melanocortin receptor ligands
  • Cyclic peptide melanocortin receptor ligands

Examples

Experimental program
Comparison scheme
Effect test

example 1

H-His-Arg-c(Cys-D-Ala-His-D-Phe-Arg-Trp-Cys)-NH2 (SEQ ID NO.:2)

[0145]The peptide was assembled using Fmoc-chemistry on an ABI 433A peptide synthesizer (Applied Biosystems, Foster City, Calif.) at the 1.0 mmole scale. The reaction vessel containing 1350 mg of 0.74 mmol / Rink Amide MBHA resin (Novabiochem, San Diego, Calif.) was placed in a reaction vessel. The resin was then treated with 10 ml of NMP for 15 min to swell the resin. The ABI FastMoc 1.0® protocol was used to generate the peptide. Each cycle comprised of deblocking the N-terminal Fmoc using 20% piperidine followed by extensive NMP washing. Pre-packaged 1.0 mmole cartridge of each amino acid was then dissolved in 0.45 M HOBT / HBTU and transferred to the activation vessel. Two more 1.0 mmole amino acid cartridges were dissolved and transferred to the activation vessel for a total of 3 equivalents of amino acid used per coupling step. A 3 ml of a 2 M DIPEA solution, was then introduced to the activation vessel for a total of ...

example 2

Ac-2-Nal-Arg-c(Cys-D-Ala-His-D-Phe-Arg-Trp-Cys)-NH2 (SEQ ID NO.:1)

[0147]The peptide was assembled using Fmoc-chemistry on an ABI 433A® peptide synthesizer (Applied Biosystems; Foster City, Calif.) at the 1.0 mmole scale. Approximately 1350 mg of 0.74 mmol / Rink Amide MBHA resin (Novabiochem®, San Diego, Calif.) was placed in a reaction vessel. To swell the resin, it was treated with 10 ml of NMP for 15 minutes. The ABI FastMoc 1.0 protocol was used to generate the peptide. A cycle comprised of deblocking the N-terminal Fmoc using 20% piperidine followed by NMP washing. A 1.0 mmole cartridge of each amino acid was dissolved in 0.45M HOBT / HBTU and transferred to the activation vessel. Two additional 1.0 mmole amino acid cartridges were then dissolved and transferred to the activation vessel for a total of 3 equivalents of amino acid per coupling step. Approximately 3 ml of a 2 M DIPEA solution was introduced to the activation vessel resulting in 6 equivalents contained therein. The res...

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Abstract

The present invention is directed to compounds according to formula, (R2R3)-A0A1-c(A2-A3-A4-A5-A6-A7-A8-A9)-A10-R1, wherein the definitions of A1 to A10 and R1 to R3 are provided in the application, and pharmaceutically-acceptable salts thereof, that act as ligands for one or more of the melanocortin receptors, to methods of using such compounds to treat mammals, and to pharmaceutical compositions comprising said compounds.

Description

BACKGROUND OF THE INVENTION[0001]The present invention is directed to peptides which are ligands of one or more of the melanocortin receptors (MC-R), the pharmaceutically-acceptable salts thereof, to methods of using such peptides to treat mammals and to useful pharmaceutical compositions comprising said peptides.[0002]Melanocortins are a family of regulatory peptides which are formed by post-translational processing of pro-hormone pro-opiomelanocortin (POMC; 131 amino acids in length). POMC is processed into three classes of hormones; the melanocortins, adrenocorticotropin hormone, and various endorphins (e.g. lipotropin) (Cone, et al., Recent Prog. Horm. Res., 51:287-317, (1996); Cone et al., Ann. N.Y. Acad. Sci., 31:342-363, (1993)).[0003]Melanocortins have been found in a wide variety of normal human tissues including the brain, adrenal, skin, testis, spleen, kidney, ovary, lung, thyroid, liver, colon, small intestine and pancreas (Tatro, J. B. et al., Endocrinol. 121:1900-1907 ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K38/12C07K7/64A61P3/04A61P29/00A61P1/00
CPCC07K14/685A61K38/00A61P1/00A61P3/04A61P5/06A61P29/00
Inventor DONG, ZHENG XIN
Owner IPSEN PHARMA SAS
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